


Now You Step Inside, But You Don't See Too Many Faces

by NidoranDuran



Category: RWBY
Genre: Anal Sex, Bisexual Male Character, Blow Jobs, Crossdressing, Cunnilingus, F/M, Feminization, Gangbang, M/M, Multi, Plot What Plot/Porn Without Plot, Prostitution, Rimming
Language: English
Status: Completed
Published: 2021-02-01
Updated: 2021-02-01
Packaged: 2021-03-12 11:01:54
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 5,380
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29134494
Author URL: https://archiveofourown.org/users/NidoranDuran/pseuds/NidoranDuran
Summary: The girls of Team RWBY tohught it would be fun to make Oscar wear a maid dress and talk about how girly he looks, but with a Schnee Dust Company board meeting in five minutes and no maid to 'entertain', Oscar gets dragged in as Olivia, and is about to discover how much fun being a girl can really be. Anonymous commission.
Comments: 1
Kudos: 22





	Now You Step Inside, But You Don't See Too Many Faces

"You make a cuter girl than some of the actual girls I've said look cute," Weiss said, nudging at Oscar's hair and adjusting it with a slightly overbearing presence that had Oscar squirming about fitfully under her touch. "And you fill this maid costume out perfectly! I didn't even know that when I pulled it off the raid, I just thought you'd look nice in it."

"You've got a really nice butt," Yang said, coming up from behind and giving Oscar's cheeks a squeeze. "It's almost as big as Blake's." Her snickering and prodding came with lots of touches that pushed a bit further than the other girls' touches did.

Which left Oscar increasingly confused over all of this. Team RWBY were all over him, prodding at him and shoving him into a traditional black and white maid outfit, insisting he even wear frilly panties they stole from Weiss's older sister's room. Fortunately, they hadn't yet lifted the skirt up to ogle his cock straining against said panties, so he was at least given some modesty, albeit a very shaky and uncertain modesty he didn't know for sure was going to actually last for very long. His shifting, wriggling frustrations could were only going to rise as he tried to make sense of this all, and Oscar was simply unable to handle the attention. Especially after they put ample amounts of make-up onto him to make him look even girlier.

"Your waist is so slim," Ruby said, slipping in from beside her sister and running her hands along his figure.

"And your hips are wide. I should be mad about the comparison to my ass, but Yang's right." Blake was a bit more stoic in her speech, but even then, the way she grabbed at him was hardly tender or controlled. She felt him up, letting the way she spoke so flatly in fact cover up the boldness of her approach a little bit, teasing and winding up poor Oscar with attentions that had him wriggling about in frustration.

"Nobody would ever know you're a boy," Weiss said, and the other girls all agreed and nodded about, eager to second the utter insanity of what they had done to him and forced him into.

Before anyone could muse much further on it, the door swung open. "Miss Schnee! One of our maids just quit, and your father has a board meeting in five minutes. Do you know anybody who needs a job?" One of the assistants to her father had burst into the room, his eyes wide with the kind of mortal panic that said his job was on the line. "We don't need a permanent position, just someone to handle the meeting, they can be paid for the hours."

All eyes slowly turned toward Oscar with an excitement and a gleeful, greedy burning that made him steadily rise in panic and concern, frustrations hitting him hard as he looked around at the girls. "My friend Olivia is right here," Weiss said. "I think she'll do great, don't you, Olivia?"

Before he could answer, there were hands pushing him on and dragging him to the board room. He was hired.  
*************************  
"This is Olivia," the assistant said, bringing the flush and shifting, nervous Oscar into the room. "She's our new maid hire, a friend of Miss Weiss Schnee."

Oscar had little idea why this was happening, but even more frustrating was the way that people began to openly murmur about how cute 'she' was, how they haven't seen a maid with such a narrow waisted, wide hipped figure in so long. There was plenty of open talk that seemed utterly ludicrous, that made Oscar squirm and shiver with great concern for all the things that this attention brought him, but he pushed in the cart with cold water and hot tea, and did his part to ignore everything about this.

The meeting room was full of upper management for the Schnee Dust Company, the table headed by Jacques Schnee himself. His wife Willow and eldest daughter Winter were there as well, Winter serving an 'advisory' position with the family company in addition to her military work. Past there, there were simply a lot of men and women that Oscar had never seen before, important people in the company, but both man and woman seemed to be remarking on him and eyeing him with appraising gazes and intentions that seemed utterly inappropriate and detached from anything decent or sane.

Oscar did his best to not let those concerns translate into anything. There would be money for this, at least. That was worth a lot in this embarrassing weirdness. He'd pretend to be Olivia for a little bit, sneak around in this mess, and come out the other side with some money to show for the embarrassment his friends imposed upon him. There wasn't much of a choice in any of this, so Oscar just had to make the most of it all. And fortunately, it was easy enough work; shuffling around being a maid meant mostly just filling up peoples' tea and water. It was simple work, and he could at least hug the wall behind him every time he pulled back, trying his best to avoid the reality crashing down upon him. The only hope of sense involved playing along, doing his part, and then getting out of here. On that front, it all seemed simple enough.

Then the groping started. While he leaned over to pour people tea, they would reach for his ass and give it a squeeze. Some even smacked his ass outright, including a panic inside of Oscar that he hadn't the slightest idea what to make of, but he kept quiet and didn't complain about it, squirming under the attention and frustration of this treatment. There felt like so much here that Oscar didn't have the slightest idea what to deal with, so he kept quiet, saying nothing and letting these touches happen without complaint or remark. It was fine. Everything would be fine. He just had to ignore all these focused gropes and had to brush off the shameful pulse of heat rising through his body as they touched him like they did.

For a good hour, Oscar tried not to pay too much attention to the overall discussion and focus only on the calls for refills. He brushed off all the comments about how he was cuter than the last maid. Even one remark about how they hoped Olivia 'had a better attitude'. It was odd, but it was fine. Everything was completely fine, and Oscar shook off the growing concern that wanted him everything here was not fine in ways that weren't yet apparent at all.

Around the one hour mark, Jacques cleared his throat. "I believe we should take a break now," he said, signaling for Oscar to come closer. Oscar approached with the tray, figuring that another drink was needed. Jacques opened his pants up with the other hand, belt already loosened in anticipation, and as Oscar got up close, Jacques rose, his pants falling and his chair rolling out from behind him. His hand reached for the new maid by the shoulder and pushed 'her' down. Oscar was on his knees, facing Jacques Schnee's backside, and a hand forced him face-first into the man's ass. “Eat.”

Confusion burned through Oscar with renewed intensity as he fumbled through licking at Jacques Schnee's ass hole, completely panicked and unclear as to what was happening or why. His tongue worked its sloppy motions against his hole anyway, inexperience probably getting the better of him in the process, but heh ad to try and deal with this somehow. His sloppy licks felt more panicked and confused as the hand tightened on the back of his head, and raw insistence kept him hopeless. Oscar had no idea what this was or what to do about it, but his tongue responded without the luxury of being able to stop, insane as this was.

"I usually screen the maids before a meeting, this was a special circumstance. You'd best impress, you can consider this to be your interview today." Jacques groaned and pushed harder back. "Olivia, was it? You're certainly cute enough to stay." He laughed, and much of the board joined in, finding nothing wrong with the sight of the boss forcing the new hire to rim him. Oscar had no idea what to make of any of it, but he wasn't given much of a choice. Everything about this wicked treatment felt like suffering, felt like a pressure and a passion that kept burning him up. Nothing sensible, not calm. Only the steady march into complete insanity.

His tongue kept licking, if only as a defense mechanism now for the weird tension and bizarre fever of giving in. Oscar had no choice but to keep going and hope for the best. What was the best? At this point he didn't even really know what he was hoping for, and the frenzied panic and heat of this treatment left him with ample questions and concerns, and no good way to make sense of any of it. Everything he did felt like pure acceptance, an embarrassing shove into all the things he couldn't make sense of, and the pleasures built messier, stronger, so hot that he just couldn't help himself anymore. He was determined to make sense of this, even if this didn't make a shred of sense to him at all.

He kept his part up even under the weight of this complete confusion, only stopping when, with a hard groan, Jacques gave in, cumming onto the table and slamming his hand down onto it. "The new girl can keep her job," he said, briefly grinding his ass in Oscar's face before letting him pull back.

Oscar hoped a bit of space would be good, hoped he could start asking question or even just run away from this all and abandon the bizarre situation upon him. There was a lot going on and he could use the space. He didn't get the space. Instead, he got a whole bunch more genitals shoved into his face. Cocks and pussies and asses. Pants were down around ankles and skirts hiked up around waists, everyone wanting a turn with 'Olivia' now and showing little hesitation in seizing that opportunity. "Wha--" was all he got before someone shoved his head between their legs, and he started blindly eating pussy, coping with the utter confusion and fever of this situation by just doing what he could to make sense of this all. Everything burning Oscar up came with such ferocity and biting fever that all he could do was try to eat this woman out and sate the strange desires and commotions overwhelming him.

He didn't know how to eat pussy any more than he knew how to eat ass. When his head was jerked back, it seemed almost, briefly, like a mercy and a chance for him to calm down, only for a cock to ram its way down his throat instead. Oscar received no such calm, struggling instead to deal with how aggressive everyone was upon him and how fiercely these pressures built. The people mobbing around Oscar tugged him every which way, forcing him to go down on them before he found himself dragged over to someone else, blowbanged by the board and left a complete mess struggling with dizzy fever to make sense of everything that kept on aching through him.

There were plenty of tugs at his hair, plenty of comments on what a pretty girl he was that added to the pressure and continued worries keeping him in a position he could do absolutely nothing about. He kept sucking and eating out the people who shoved their ways into his face, a pleasure growing stronger and fiercer. Little hesitation, little pleasure. Wild, feverish spectacle kept swinging up harder through him, his confusion abounding and an aimless degree of complete fever sweeping without a shred of normalcy. Lightheaded fever and a dizzy, fumbling pleasure kept Oscar in place, unable to argue against this and lacking in any sensible way to grasp this. He was simply stuck there, stuck trying his best to deal with the feelings that kept hitting.

He started getting them off, and the taste of cum flooding his mouth should have been a moment of panic for Oscar, should have been the point where he started to zero in on just how much this was an over the line mess he kept falling deeper into, struggling to grasp all the ways these sensations bullied him into submission. He was giving in to all of this, still not complaining, still not standing up for himself, and now he was getting people off, bringing them to orgasms that he had to drink down the mess of as he continued his hopeless service, licking wildly, tending to cock and pussy without help, occasionally, eating some ass and getting laughed at harder as he continued his descent.

Finally, having gotten off a dozen people, face covered in semen and pussy juice, he was given a moment of calm, dizzy and baffled as he looked up at them.

"Was this your first blowbang, Olivia?" Winter came up from behind him, hands on his shoulders, gently teasing at him as she came into place.

"Yes." Why was he answering so directly? This was insanity, and Oscar felt like he should have done something to fight this off, should have avoided falling deeper into this mess. But he didn't try to explain anything. Just panted and shivered back and forth, cum dripping from his lips, a hopeless expression spread across his face.

"You'll learn better for next time." Winter grabbed Oscar by the hair and tugged him up over the table, pulling his dress up, her eyes flashing in panic and recognition at the sight of the panties he had on. Those were her panties. "Where did y--" She stopped. There was no way they had been taken from her room, right? It was fine. She cleared her throat, tugging his panties down over his ass. "Now, let's get this girl’s ho--" She stopped again, this time even more abruptly.

Dangling very clearly between the lap of the maid named Olivia was a cock and balls. Everything came apart immediately, people starting to murmur amongst themselves and questioning what they saw.

"I-I'm not..." Oscar wriggled. Finally, the shame got to him. "My name isn't Olivia. My name's Oscar, I'm a friend of Weiss and they thought this was funny t--" A firm swat across his cheeks made him yelp and stiffen up, shocked into sudden panic and silence.

"No," Winter said. "No, you're still Olivia." On that note, she shoved forward, burying her face into Oscar's ass and catching him wholly off guard instead, holding him down and devouring his ass with frenzied motions and attentions that shook him quickly to his core. Oscar had been going down on everyone, but now someone was touching him, his body unsure how to respond to it. The tongue pushed its way against his hole, and his head rolled back. Winter was going to town on him, possibly trying to show him up by proving to him what a real rimjob was. But even if she was trying to passive-aggressively show him up, the pleasure of letting her dive in and devour him was winding him up for incredible delights he just couldn't fight.

"You're still Olivia," someone said. "And you're still a girl. A girl we're going to fuck like every other maid." Confusion and embarrassment seared harder through Oscar as the pleasures wound up, as the continued pressure and attention of that shameless tongue burying its way into him. The desperation and pressure that followed was something as reckless and as greedy as could be. He kept moaning in dizzy, aimless response, struggling to handle the growing chaos and confusion that burned through him. He didn't have a good way to handle nay of this, struggling to grasp even the slightest mess of these senseless pleasures. he just had to take it, had to accept that tongue working against his hole as he got eaten out in front of all these people. His pleasure was the centerpiece of this moment, a treat as depraved and chaotic as could be.

To squirm and wriggle in fitful panic was more embarrassing and exposing than going down on people had, but Oscar remained a panicked, fever mess taking the tongue and losing himself to jut how hard this all hit. He was powerless against it, wishing for clarity that didn't come. Instead, he fell further, gripping the table and gasping out in the confusion and panic. He was stuck taking on pleasures and worries that increased in demand and fever. Oscar couldn't believe this was all happening, but his failures to express anything even slightly calming to spare him this embarrassment continued to compromise his thoughts as the tongue kept pushing on, toying with his hole and demanding so much from him.

Unable to contain himself, Oscar came, and he came hard, cock erupting all over the table in a messy show of sticky, gooey chaos. he couldn't help himself. He whined, he bucked, and the cutest noises spilled from his throat as he surrendered fully to pleasures and passions too wild to control, unbelievable joys sweeping up through him that didn't feel like they could be helped. It was just what he needed, and the delight of submitting to these conquering passions. Oscar didn't know what to say, hips wriggling about, his cock pulsating as all the eyes upon him seemed to only grow firmer. There felt like no escape and no sense, but for the first time since this all began, Oscar found himself oddly ready for that, and oddly okay with the idea.

A cock slipped into his ass before he could say anything, the shocking weight of sudden penetration and passion leaving him shaken to the core. "You're too pretty not to be a whore," the man groaned, as his hips pounded into Oscar without hesitation, and the role of Olivia was one he was going to have to play. Suddenly, that felt a lot more okay though, his body thrashing and wriggling under the wild passion and weight of getting filled by cock, fucked with deep, purposeful strokes and an intent that he had no way to process. "M-my pussy needs your cock!" Oscar shrieked. Why was he doing this? It didn't matter. He was into it now, a moaning, dizzy wreck jerking about, fucking back against the powerful thrusts that shook him. He should have tried to do something to balance himself out and control all these strange passions, but instead, he fell deeper.

"You're such a cute slut," the man growled. He pushed Oscar up further, drilling his hole with greedier heat. "Look at this bitch take it. She's so cock hungry." Everybody seemed so ready to give in. They cheered on for him to fuck the new girl, treating Oscar as Olivia and continuing on with the depraved heat and escalating panic that didn't want to stop. There was so much to try and deal with her, and soaking in all these pleasures came at a strange cost. Endless gangbang pleasures if he went along with being a girl. It sounded insane. It felt insane. But Oscar couldn't help it. He took the thrusts, throbbing under the wild eruption of sensation and heat that kept hitting, desperate to give in deeper and harder to the pure joy of giving in. It was everything to him now,

"I love being a slutty girl," he whined, giving in to this harder. The overwhelming passions and delights that continued to push her limits all felt so bizarre and so frenzied that it didn't make a lot of sense to him. He just kept giving into it, and the more that it pushed him, the better he felt. Oscar needed this, craved the hopeless plunge into delight and depravity that came from feeling the thick cock railing him, all while his cock dripped and begged in neglected panic and delight, depraved heats rising up through him. He couldn't handle any of these feelings properly. His inexperience caught up with him, left him dizzy and frantic and completely detached from anything approaching sense.

But it felt so good, and the more he let it sweep through him, the hotter Oscar felt. He looked at the board members all standing there, waiting their turns, stroking and fingering themselves in wait. He couldn't believe his eyes, couldn't believe the wild frenzy of what hit him. He was in the middle of all this, the popular presence getting used harder, and the way people spoke so intensely of his looks said that they really believed he was a pretty girl. That he was worth buttering up and fucking. It transcended sense, but the idea of slipping into a feminized role of cute girly fucktoy for these powerful people appealed to Oscar more intensely than it had any right to.

Getting cummed inside of pushed him over the edge, made him shudder, twist, writhe under pleasures and senseless delights as ferocious as could be. He felt amazing, and the relief coming over him left him truly floored, whining and whimpering over the table as he gave in again.

Hands seized his hips and rolled him over onto his back, flipped around with his legs up in the air. Someone came in from below and pushed their face into his ass, nose rubbing against his balls as they began to eat him out, but before he could look at who it was, he had a pussy pushing down against his face. There was no time to respond to any of this as he got his face sat on, remarks of, "You're such a good whore," proving the insistent push he needed to just give in. He kept licking and fumbling about, letting himself succumb to every last bit of intoxicating pleasure that had already proven would be his undoing. His tongue went right into the frenzied pace and fever of trying his best to deal with all of this, making the most of pleasures that didn't want to quit.

The tongue sloppily and indecently toying with his ass kept him panicked and needy. Nobody touched his cock. He doubted anyone was going to as he remained the 'girl' in this situation, fumbling deeper into clumsy and confused heat. The pleasure didn't let up for a second. It was so much in all the best ways, double-teamed and greedily laid into with so much aggression and pleasure that his only choice was to succumb. He whined and wriggled on the table, letting the pleasures keep challenging him. He wasn't in a position to do anything but fully surrender, and he welcomed the chance to fall further and further away from sense, giving in with all-eclipsing fever and a passion too wild to believe. He felt great, as insane as it was, and the more that Oscar wanted to let this dominate him, the happier he felt. 

There was no end to this weird chaos, to the pleasures that continued to burn through his body. He pushed all of his energy into the sloppy, hopeless, frenzied oral he gave the woman riding him, who ground against his face and pinned him down to the table, using her whole body's weight to hold hi in place and use him hard. There was nothing Oscar could do but accept it, falling deeper into pleasures that felt too ecstatic to be real. He felt completely, hopelessly dominated now by this pleasure and by whatever the board members wanted to do to him, and as long as he could stumble his way deeper into this, he would be feeling great. Nothing to do but fall further and allow pleasures to rip him asunder.

He came hard, cock jerking and twitching, cumming all over his stomach as the tongue in his ass worked in tireless passion against him. He let it happen, lost to the frantic pleasures that continued to insist upon him their harshest demands. He was lost to these pleasures, unable to rationalize the way these pleasures kept him falling further and further away from sense. He ate the woman out to her own orgasm, not even sure he was succeeding until she crashed into the pleasure and completely fucking gave in, losing herself all too happy and giving up to it all, the ecstasies burning stronger. It was too much, and the pleasures remained insistent upon him as he burned in a shaky, shivering afterglow.

There was no time to bask, though. Hands tugged him up, and he found himself getting pulled down on top of Willow. "Come rest on me, little girl," she moaned, grabbing his cock and slamming him into her. "I love letting my husband fuck nasty, girly sluts like you on top of me."

That was all the warning that Oscar got for the harsh slam of Jacques's cock right into his ass. But fortunately, that was all the warning Oscar needed, receiving the senseless pounding of his ass that swept up through him. The pleasure was ferocious and it was unbearable, demanding so much that felt like it was going to wear him down completely. He was stuck in a weird position here, sandwiched between the married parents of one of his friends. Of the girl who stuffed him into a maid dress in the first place. If only Yang knew that her efforts to tease him had led to him getting used to spice up her parents' marriage. He had no idea what to make of that, and he struggled harder under the incredible weight of this all, jerked about back and forth with absolutely no idea how to make sense of it.

His cock received the first attention it got in all of this mess, thrusting into Willow's pussy with the helpless passion and speed imbued upon him by the ferocity of Jacques and his downright savage thrusts. This was way too much for Oscar to conceive of, his struggles hastening his crash as every wild push into pleasure demanded just a bit more from him. He felt oddly hot at the mercy of this merciless, senseless pleasure, stuck in a situation where nothing about this really made a lot of sense, but he kept taking it, kept giving in and allowing himself to fall further. His wild motions back and forth left him dizzy, frenzied, struggling harder to deal with the pleasures that kept rising. The tension it all built up in him was otherworldly, and the sensations kept him lost, dizzily heaving back and forth through something unbelievable.

Every slam down into his ass was a harsh reminder that submission was everything he needed, and the more that Oscar gave in, the better he felt. Jacques drilled him without patience or calm, and the thrill of giving up weighed heavier on Oscar as he fell further and further along. It didn't slow down, didn't soothe its demands for a moment, but that was more than okay by him. He felt better and better as these pleasures took their savage course on him. Every thrust into his ass came with a thrust down into Willow. His body felt like it was being controlled entirely by their own demands, his every motion dictated by what they wanted from him. He felt oddly happy to succumb, happy to fall deeper into these joys and sink further and further into passion. It was too much, and he knew another eruption into joy was imminent.

This time, all three came together. Oscar was a bit too dizzy to tell if anyone was a bit faster; he was simply too far gone to understand it, to grasp in any real capacity what was happening aside from the burning pleasure. The warmth pumping into his ass. The tightness of Willow's pussy begging around his cock. The gooey joy of cumming in Willow in turn, his balls tightening and his cock tingling in delight as he felt just that bit more tired, but it didn't matter. He needed it. He craved it on a level too grand to be able to help. It was everything he wanted, and the ecstatic joys of giving in were so beautiful and so hot that he just felt like he was getting more and more of everything he needed, perhaps to a degree he wasn't ready to keep facing.

Back on the table he went. Off the table. Into someone's arms and off the ground entirely. Oscar couldn't keep his head on straight as all the pleasures tugged him in a million directions at once. At some point, he was riding one cock cowgirl style and smacking two cocks down onto his face and his out-rolled tongue, begging for them to treat his slutty throat to the hardest pounding they could. He shrieked about how much he loved being a slutty girl while getting pile driver fucked on the ground. Every position felt like an expression of some new form of madness, all the while being treated to pleasure beyond sense. Everything kept hitting him, and he kept taking it, dizzily reveling in the idea that he could get fucked stupid and love every second of it so strongly. It was simply too good to resist.

At the end of it, he was on his knees, whining as he got everyone jerking off in his face one last time. Men stroked their cocks, and the women who could squirt rubbed shamelessly at their pussies, ready to grant one final christening of the slutty new maid Olivia. He was ready for it, eyes rolled back, mouth open, the pleasure coming on in a ferocious bukkake as reckless and as overwhelming as could be. There was little sense to any of this, and he welcomed it. The rain of fluids onto his face was simply the cap onto everything that followed, and he almost collapsed to the floor, exhausted by overjoyed, a look of indecent delight on his face.

The board meeting continued. Oscar lay on the floor, half passed out, dress tugged up, cock soft at his thigh. It didn't matter. They finished running down the agenda as though a gangbang hadn't just taken place, and then ultimately parted ways, Jacques looking down from his chair toward the still-present femboy lying happily there and musing, "What to do with you, girl?"  
***************************************  
"He's got to be around somewhere, right?" Weiss was concerned as she walked around the house with Whitley, both of them trying to find Oscar. Weiss's friends had all left, but they hadn't seen Oscar in hours, and with them seen off, Weiss was able to pivot all of her concerns to the idea that somewhere, Oscar had to be somewhere. She ultimately decided Winter was the one to ask, figuring something had to have happened at the board meeting, and Winter would surely know everything.

What they found was Winter bending Oscar over the bed, drilling his fat ass with her strap-on.

"Not fair, you said you'd fuck me!" Whitley shouted.

"That's my friend, what are you doing?" Weiss asked, equally as concerned, though perhaps for a different reason. At least outwardly; she would have loved to get pinned down and dominated by her sister's strap, too.

"Relax, father said the new maid is ours to have fun with when she's not busy with a meeting." Winter gave some firm smacks to the round ass she kept hammering into. "And as I see it, Weiss, you stuck your friend into my panties, so I get to fuck her plush ass all I want to. Now, you two can complain about it from over there, or you can get undressed, come over here, and join me in treating our new servant Olivia to all the sex she can take."

There wasn't a moment of hesitation. Weiss and Whitley bolted forward, striping down and rushing into Winter's room to play with their new toy.

**Author's Note:**

> If you enjoyed this depravity, why not follow me on twitter https://twitter.com/nidoran_duran and get updates on my new and upcoming stories?


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